Do Startup Owners Ever Truly Take a Break?

Some days, entrepreneurs can empathize with Sisyphus.

“A vacation is what you take when you can no longer take what you’ve been taking.”
–Earl Wilson

It doesn’t take much reading on this blog or talking to me to discover that I am a big fan of Tim Ferriss’s book The Four Hour Workweek. I remember browsing through the Barnes and Noble (before showrooming became popular), seeing his book, and becoming intrigued. A cup of coffee and a bunch of pages later, I was hooked and bought it.

Recently, I had drinks with a friend who is in a similar situation as we are, and he was talking about the book and complaining how most of the people he knew who read it misconstrued what Ferriss was really talking about with that book.

The book isn’t about working 4 hours a week and then kicking back in your recliner with your feet up on the ottoman drooling at your 183” flat screen TV all day.

However, the premise in the title of the book is also pretty darn appealing. Build a business, automate, set it up to where it runs, check in occasionally, and voila! A four hour workweek.

I had those visions of sugar plums dancing through my head when we started up our company. At our first corporate retreat, we discussed, appurtenant to the required hockey stick chart of profits, how we wanted to eventually have a company that ran itself and paid out the dividends for us to live royally off of while we went out and did the things that we really wanted to do.

We’d be the professors emeriti of our company, or the “of counsel” of some law firms without the semi-firing that accompanies that title. Once in a blue moon, we’d emerge from the mountain to issue an edict of brilliance which our company would take as gospel, and go forth and make it happen. We’d go back to our laboratories of creation of the things which truly interested and inspired us, and tinker again.

In a sense, freedom from work was freedom to work.

It’s one definition of financial independence – the ability to work on what you want to because you no longer have to work to pay the bills. It’s oftentimes both spiritually and financially rewarding.

However, the grim truth was that we were nowhere near that point. The halcyon days were some speck of light far in the future, indiscernible from the thousands of other specks of lights which represented our potential outcomes.

Most of those specks, let’s be honest, were oncoming trains.

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So, to achieve that dream of being the idle men, we had to work. We had to hustle. We had to convince people to hire us to do things while not becoming engulfed with “buck scent”.

You work on your business so much that your subconscious can’t help but notice that something big is going on up there in the front of the mind.

It wants to pitch in. This isn’t the Monkey Brain version of pitching in. This is full brain engagement I’m talking about.

It’s the type that has ideas zinging into your conscious thought at all times.

The first time I took a real vacation after starting the company, we went to Italy. You’d think that going to Italy would be far enough away, geographically and culturally, that I’d be able to forget the company and focus on the trip.

You’d be wrong.

Even with limited Internet access and no phone communication, I did what I could to check in.

The same happened when I went to South Africa.

Even on our 10th anniversary in France, I would surreptitiously (or not so surreptitiously) pull out my iPhone and look for wifi hotspots to try to check mail, and I’d catch up on e-mails when we were on the train, queueing my responses up for the next time I could find a free wifi hotspot to sync up again.

Once my sale was finalized, I finally had a vacation where I didn’t think about business at all.

I’ve taken some vacations since starting Hull Financial Planning. I really, truly thought that since the circumstances of this company were much different than the circumstances of founding my previous company, I’d be able to get my mind off of work and onto vacation. After all, this was a mixture of capitalism and passion, not just a pure play of capitalism like the last company was.

It got worse when we went to Colorado. I read a slew of articles and papers related to the field and came up with a ton of ideas about blog topics and ways to serve clients (including, yes, this article). I was constantly reading and tinkering. I’d get up earlier than my wife, make coffee, sit in front of an open vista overlooking Mount Meeker and read geeky articles about psychological research and brain testing.

It took several days to really, truly unplug. About the time I unplugged, we were on a plane headed back home.

The lack of unplugging this time has had a much different tone to it than in my previous company. Previously, it was the “ohcrapeverythingisgoingtofallapartifidon’tkeepmyhandsonthewheel” over-obsession with thinking that I needed to do things to ensure that revenues kept coming in or a customer didn’t walk away in a huff. This time, it was my mind spinning out ideas and me reading things which truly interest me – lack of unplugging coming from a source of inspiration rather than from a source of need. The difference was astonishing, and even though I really didn’t mentally divorce myself from the vacation, I came back refreshed and ready to go.

At some point, I’m sure that entrepreneurs who stick with it have businesses that graduate from startup to sustainable. Maybe then they can unplug more. I know I didn’t, even when our company reached that point of sustainability when we could assuredly say that we were going to survive another year.

Here’s what I’ve learned about unplugging from my mostly failed attempts to do so:

Go for longer than you think you need to. I’ve generally taken one week vacations, with my two trips to southern Africa as the exceptions. I’ve found that my brain stops racing by about day 5, and I’m pretty much into a new pace by about day 7. That’s usually when I’m on a plane back home, defeating the purpose of trying to unplug in the first place.

Practice with a staycation. If you work from home, this will be more difficult to do, but see what happens when you’re not in the office. Do things get done? Can your company still deliver value to customers? It’s also a good first trial run to see how things work when you’re not there. You can often find the holes in your company through an enforced absence, even if it’s only the veneer of an absence.

Leave the electronics at home. I’m really bad about this. I like my iPhone, even if it’s still the old-fashioned 3GS version which is slower than a 100 meter mosey contest. When you depend on technology for entertainment and connectivity, it’s oh-so-tempting to just sneak in a “few minutes” (or so you tell yourself) to check in and see how things are doing. Once you’ve broken the seal, you can’t go back. So, just leave it at home in the first place. I’m sure my wife will bash me about the head and shoulders with this bullet point next time we go on vacation!

Napoleon once said that his only wife was the military. He also said that soldiers would do anything for baubles, which explains the prevalence of gamification. Startup founders can understand the Napoleonic sentiment about being married to the profession. Whether or not we intend for it to, few of us can really divorce ourselves from our startups, even if we physically remove ourselves for a while.

It’s something to be aware of, and something for married entrepreneurs to gird their spouses for. If you don’t do it right and budget enough time, as well as taking away your gadgets, you may as well not go on vacation because you’ll be wasting your time thinking you should be back in the office and your money because you’ll be paying to go somewhere else to do the things that you would be doing had you never left home in the first place.

Are you an entrepreneur who’s been able to unplug on a vacation? What did you do? Alternatively, does my story sound eerily too familiar? Tell us about it in the comments below!

The Winning With Money course offers 20 lessons, 8 worksheets, and several exercises designed to provide you with the answers you need to have certainty in your financial life. Stop spinning your wheels and take action!

Jason Hull, CFP®, is a Fort Worth financial advisor. Before becoming a Fort Worth financial planner, Jason co-founded, built, and sold a software development company. He has a MBA from the University of Virginia, and a BS from the United States Military Academy at West Point. He is the owner of Fort Worth financial advisor Hull Financial Planning.

Comments

“This time, it was my mind spinning out ideas and me reading things which truly interest me – lack of unplugging coming from a source of inspiration rather than from a source of need. ”
Great sentence, Jason– I think you’ve just described my last decade of retirement!

Doug–You’re a great example of what I’m talking about. You could have spend the rest of your life on a longboard surfing away, but you’ve channeled what’s important to you – helping out the military and veterans – and continued to find meaning. You retired to something. I don’t know enough of your Navy career to say whether or not you retired from something, e.g., to get away from the Navy at 20 rather than face another day of flying a desk or something similar, but, in the past decade, you can truly say that you retired to something as you continue to give back. It’s a much more enriching life, and, furthermore, it’s a lot of fun when you can turn your subconscious onto tasks which truly interest and intrigue you rather than whatever the next Dilbertian project is.

This article was so fantastic that I want to leave a comment that’s more meaningful than simply, “great post.” Yet I can’t think of what to say. You’ve said it all so well — that entrepreneurship demands long days, opportunity cost, and the risk that this may all be for naught; that when we do take vacations, our minds are still engaged; and that the only way to break free is by disciplining ourselves to do so.